Citric Acid → 1,3-Propanedione, 2-ethyl-1,3-bis(4-methoxyphenyl)-

HRID 2087012Notes

Reaction equation

HRID 2087012 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:12](O)(=O)[CH2:13][C:14]([CH2:19][C:20](O)=O)([C:16]([OH:18])=O)O>C1COCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:1](=[O:10])[CH:1]([CH2:2][CH3:3])[C:16]([C:14]2[CH:13]=[CH:12][C:5]([O:8][CH3:9])=[CH:20][CH:19]=2)=[O:18])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 7477p-Anisoyl chloride

Product 1

HCID 1353051,3-Propanedione, 2-ethyl-1,3-bis(4-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4′-methoxybutyryl phenone (1.0 equiv.) in THF at −78° C. was added dropwise 1.5 equiv. of [(CH3)2Si]2NLi. The solution was stirred for 1 h at −78° C., followed by addition of 1.2 equiv. of p-anisoyl chloride. The reaction mixture was stirred for 10 min at −78° C. and then for 22 h at rt, acidified with 10% citric acid, and extracted with EtOAc. The combined organic layers were washed with water and dried over Na2SO4. Removal of solvent in vacuo provided a crude solid which was purified by flash chromatography (CH2Cl2) to give 1,3-bis(4-methoxyphenyl)-2-ethylpropane-1,3-dione.

Workup

  1. stirringThe reaction mixture was stirred for 10 min at −78° C.
  2. waitfor 22 h at rt
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of solvent in vacuo
  7. customprovided a crude solid which
  8. customwas purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-a2287fcfdd774c9db9a0ee2e776d35a4
Source dataset
uspto-grants-2004_04
Patent number
US06727273B2

Reaction notes

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